Lawrence O’Donnell

The ongoing battle between cable’s Fox News and MSNBC sometimes makes TV’s Ultimate Fighter seem tame. MSNBC’s latest weapon is Lawrence O’Donnell, one of the gutsiest, most fiercely intelligent and entertaining hosts on any television network, cable or otherwise. So when ratings king Keith Olbermann parted company with MSNBC, O’Donnell was the natural choice to fill his chair.Each weeknight on his show, The Last Word With Lawrence O’Donnell, the host, who is so far to the left of the political spectrum that he has described himself as a socialist, discusses the issues of the day—clashes between unions and state governments, Afghanistan, Charlie Sheen—with a sharp focus on what he calls “Republican folly.” He delights in skewering conservative media figures and politicians. He called Vice President Dick Cheney’s speech on counterterrorism policy “sleazy.” He slammed Fox News commentator Glenn Beck’s “fake biblical literalist piety.” He has criticized Minnesota Republican congresswoman Michele Bachmann’s “breathtaking demonstrations of ignorance levels previously unimaginable in a member of Congress or a graduate of an ­American elementary school” and has called Fox’s Bill O’Reilly “a joke” and a liar.

O’Donnell, who is from Boston, is to the political left what O’Reilly and Rush Limbaugh are to the right—that is, if either were also a Harvard graduate and political wonk versed in the minutiae of health care policy and tax codes. After college O’Donnell worked for half a decade, first as communications director and later as senior advisor, for Senator Daniel Patrick Moynihan, who once said of O’Donnell, “He’s maybe the smartest man, and he sure as hell is the toughest.” In addition to his inside-the-Beltway political career, O’Donnell, who is 59 and married to actress Kathryn Harrold, has written a book, worked as writer and producer on the TV show The West Wing and acted on that show and on Big Love (he had a recurring role). On MSNBC, he guest hosted Hardball With Chris Matthews, The Ed Show, The Rachel Maddow Show and Countdown With Keith Olbermann, which led to The Last Word.

Playboy sent Contributing Editor David Sheff, who conducted last month’s interview with Congressman Barney Frank, to New York to talk media and politics with O’Donnell. Sheff reports, “O’Donnell is the rare television host who talks beyond bullet points about almost any issue you can name. Ask him about health care, and along with analysis of the Obama plan you get a detailed, nuanced history of the issue as it has evolved since the Nixon presidency. O’Donnell seemed sincere when he said he prefers serious debate to the kind of shouting matches many cable news hosts are famous for, but that didn’t stop him from ripping into former House Speaker Newt Gingrich, who that day gave an interview in which he blamed his marital infidelities on his passion for America. O’Donnell, on a tear, said it had less to do with Gingrich’s passion for America than it had to do with Viagra.”

PLAYBOY: As a former advisor to a U.S. senator, do you ever feel it’s unseemly to be part of the sparring on cable news shows?O’DONNELL: It’s the nature of these shows. In its successful form, prime-time cable news is op-ed television, which is why CNN usually runs last.

PLAYBOY: Does contentiousness drive ratings?O’DONNELL: My highest-rated shows were 25 minutes with the vice president, which was not contentious in any way, and any 10 minutes I’ve had with Bill Maher, which were not contentious either. Contentiousness is not what drives the ratings.

PLAYBOY: Yet lots of yelling goes on. Bill O’Reilly is famous for interrupting guests and sometimes bullying them.O’DONNELL: I don’t think it’s required. The audience is drawn to someone who gives voice to how they feel. It doesn’t have to involve yelling or bullying. But I do think it’s probably satisfying to his audience to see O’Reilly beat someone up.

PLAYBOY: You’ve attacked O’Reilly, recently for his interview with President Obama. What was wrong with it?O’DONNELL: You have your big Super Bowl moment to interview the president and don’t ask a single memorable question, not one, other than “How does it feel to be hated?” And this was coming from someone who is hated by millions of people. It’s a stupid question because it’s one you could ask any president. They’re all hated. In fact, Obama is hated in lower numbers than most presidents. O’Reilly didn’t ask one worthwhile policy question. He had an interview opportunity with the president, and he completely blew it.

PLAYBOY: You once said of O’Reilly, “I see dozens of guys I grew up with who are just like him—overbearing, argumentative Irish guys.”O’DONNELL: I can’t take Bill seriously. He’s a character I’ve known since I was a kid. He makes me laugh more than anything else, because he’s this faux character, a character he plays in a series called The O’Reilly Factor—the braggadocio Irish guy who plays as if he’s smarter than you, but in fact he doesn’t know very much and can’t really back up what he says. Everybody from my neighborhood knows that character and thinks that character is a joke. You know, the tough-guy part of it is the biggest fraud of all. Bill’s from Long Island. Sorry, that’s not tough-guy territory.

PLAYBOY: Is Glenn Beck a newer version of O’Reilly?O’DONNELL: Beck is one of the great showmen of this field.

PLAYBOY: Some people think he’s dangerous, potentially inciting viewers to violence.O’DONNELL: He doesn’t feel dangerous to me. It’s hard for a man in makeup to feel dangerous.

PLAYBOY: Do you think Beck believes the extreme views he espouses, or is he pandering to his audience?O’DONNELL: The latter. He follows his audience. He tells them what they want to hear.

PLAYBOY: So extremism sells?O’DONNELL: Well, maybe Beck’s extremism has to do with a straight decline in his audience over the past year. It’s quite pronounced. His numbers have declined. People are theorizing that it has to do with his going too far, making no sense and cheering for the wrong side—for example, cheering on Mubarak in Egypt. Another thing is that he’s a doomsday guy. “The world is coming to an end” is his thing. You can say that for a limited time, and then it had better come to an end or people will think it’s not worth listening to you much longer. [Editor’s note: Shortly after this interview was completed, Beck and Fox News announced they were parting ways.]

PLAYBOY: Does Rush Limbaugh also pander?O’DONNELL: Yes. He tells his audience what they want to hear. Even more than that, he plays the character they want him to be. Rush did a horrific physical imitation of Michael J. Fox, who has Parkinson’s disease. If we have a beloved actor in America, it is Michael J. Fox. He’s bearing his disease nobly and bravely, and you have no option but to admire him. Rush decided to attack him, though, because Fox is a Democrat. Rush did his horrible impression, with his arms moving out of control and all that. His viewers saw Rush do that and didn’t think it was funny. There’s absolutely no doubt in my mind that Rush Limbaugh deeply regrets what he did, but he will never apologize for it, ever, because the character Rush Limbaugh cannot apologize. That would destroy the character, and that’s all he is—a character, like O’Reilly and the others.

PLAYBOY: Do you worry Limbaugh and other right-wing commentators’ audiences believe them when they encourage rather than refute untruths, such as the so-called birthers’ belief that President Obama wasn’t born in the United States?O’DONNELL: To me it’s just stupid.

PLAYBOY: You angrily attacked potential Republican presidential candidate Mike Huckabee when he said President Obama grew up in Kenya.O’DONNELL: I wasn’t terribly angry about it. I just commented. He said, “The one thing I know is that President Obama was raised in Kenya.” I said, “If that’s the one thing Mike Huckabee knows, he doesn’t know anything.”

PLAYBOY: And yet some right-wing pundits continue to encourage the birthers and other Obama conspiracy theorists.O’DONNELL: Yes, the number of people in America who believe these lies would be dramatically lower if the Huckabees and Republican congressmen and O’Reillys were all sharply and clearly adamant and honest. You wouldn’t see this alarming mushrooming in the number of people who think Obama wasn’t born or raised here or think he’s a Muslim. The numbers would be far lower if people treated this the way John McCain did during the campaign. He clearly said that Obama isn’t Muslim and is an American. They’d go away if everyone treated obvious falsehoods the way Ann Coulter does. She’s adamant about the birthers being crazy.

PLAYBOY: Do the ones who fuel the flames, encouraging the misinformation, do so intentionally, manipulating their audience, or do they believe the lies?O’DONNELL: I don’t think a single Republican congressman believes there’s any issue with Obama’s birth. Not one. And I don’t believe Sean Hannity or O’Reilly or any of those people ever thought there was any issue with Barack Obama’s birth either. I don’t think anybody working at Fox News thinks that. But the thing people fear most with an audience is offending them. When you know a significant portion of your audience thinks Obama isn’t a citizen, you talk about it in a different way if you’re in the audience-preservation business or the voter-preservation business. It’s brave when someone like Ann Coulter says the deniers are nuts. She may be losing a speaking fee here or there because of it, but apparently she’s interested enough in electing conservatives to separate herself from the crazies.

PLAYBOY: How will that help elect ­conservatives? They’re the ones making the assertions.O’DONNELL: She knows you need to appeal to independents in order to elect conservatives and that when you want to appeal to independents, you do not want to sound crazy. George Will dealt with this in his column, talking about these increasing “vibrations of weirdness,” he called them, coming from Republicans and Republican candidates, and that week he labeled Huckabee the newest and worst offender of them all. Will wants conservatives to prevail electorally, and the crazier they sound, the less likely they will.

PLAYBOY: It sounds as though you don’t think Huckabee has much chance of becoming the 2012 Republican presidential nominee.O’DONNELL: [Shakes head]

PLAYBOY: How about Sarah Palin?O’DONNELL: Palin is the most recent losing vice presidential candidate who will never be president. In the television age, no losing vice presidential candidate has ever succeeded. Exactly two managed to get themselves back on a convention stage: Walter Mondale and Bob Dole. They lost. Palin knows this, and she has no intention of running for anything again in her life. She made that absolutely clear the day she quit the governorship in Alaska. She’s doing everything she should do as a moneymaking operation, which is what she is. She will never say she’s not running for president until it’s absolutely beyond obvious, because she understands the second she’s not running, Tim Pawlenty becomes more important.

PLAYBOY: Has Palin been good for commentators like you? She seems to provide an endless supply of faux pas, family scandals and shocking statements.O’DONNELL: She’s been good for us, and we’ve been good for her. We are doing everything we can to feed her moneymaking capacity by keeping her alive. What if we treated her as we did Dan Quayle? How much is a Dan Quayle speech worth right now? She is absolutely a cable news creation. There is no Dan Quayle phenomenon, and there wasn’t after he was on the losing side of the vice presidential slot. There was no Joe Lieberman phenomenon after he was on the losing side of the vice presidential slot. I think she knows that, which is why she does what she does to keep herself on our radar.

PLAYBOY: Does Newt Gingrich have a shot at the nomination?O’DONNELL: No. Newt is trying to make us French. He won’t succeed.

PLAYBOY: How is he trying to make us French?O’DONNELL: He’s trying to say three marriages are okay. At some point three marriages will be okay, but not now. Two marriages weren’t okay until Reagan came along and won. McCain had two, but he lost for other reasons. At this point, Newt cannot be elected with his marital record. I don’t care about it, but many people do. I would have voted for Mitt Romney’s great-grandfather, who had five wives at the same time, if I agreed with him on policy. I’d vote for Newt Gingrich if I agreed with him on policy. But I don’t decide the elections. People who decide elections, the swing voters, apparently care what kind of person you are. Newt’s story includes stuff that a consensus of Americans finds extremely negative. Having your wife in a hospital for cancer treatment and going in to discuss divorce terms is considered uncool by enough people, especially conservative Republicans. Also, I don’t think he can overcome the optics of running for president.

PLAYBOY: What optics are required?O’DONNELL: You can’t look the way he looks. You have to be thinner. You have to be trimmer. He would lose in the general election, absolutely, but he’ll never get to a general election.

PLAYBOY: What’s your take on Mitt Romney?O’DONNELL: Romney is going to have a problem with Christian fundamentalists who believe Mormonism is not an actual Christian branch but a heretical branch. They will not vote for a Mormon under any circumstances. I could vote for someone who married five times, and I could vote for a Mormon for anything. Tell me what your tax policy is. Tell me what you want to do with Medicare and Social Security. But Republicans, at least evangelical Christian Republicans, would have a serious problem voting for a Mormon, and they won’t. It’s why Romney gave a speech in which he tried to explain his religion. He talked about the faith of his fathers, but he didn’t say anything about the faith of his fathers. He didn’t say a single thing his fathers believed, not one. And the one Mormon he cited, Brigham Young, he cited heroically.

LAYBOY: What do you have against Brigham Young?O’DONNELL: Brigham Young said God told him that if a white person has sex with a black person, the white person will die on the spot, in the bed, won’t take another breath. The media don’t know that, and they think that because a university is named after Brigham Young and its basketball team has black players there’s nothing else to think or know about it. But if the candidate brought up the faith of his fathers, then you can reasonably ask the candidate questions about the faith of his fathers, including the fact that well into Romney’s adulthood his religion said that black men could not be priests in this church. Then, one day, the president of the Mormon church said, “God just told me he has changed his mind, and black men can now be priests.” The day before God changed his mind, what did Mitt Romney think about black men not being allowed to be priests in the Mormon church?

PLAYBOY: Who would have a harder time running for president in America, a Mormon or an atheist?O’DONNELL: An atheist would have a bigger problem in America overall but a smaller problem with evangelical Christian voters, because to them an atheist is not a heretic. An atheist is not putting a false god in front of God.

PLAYBOY: Of the current pack of contenders, who’s the most likely Republican nominee?O’DONNELL: Tim Pawlenty is the only one. It’s a process of elimination. There’s a serious problem with every other Republican running for president. Besides his religion, Romney has the problem of having created Obamacare in Massachusetts before ­Obamacare went national. In the end Huckabee probably won’t run, but if he does, he won’t have the wider appeal necessary. As I said, Palin’s not going to run. She’s a loser, and America hates losers. Ron Paul will get his solid seven percent of the vote. Pawlenty is the only guy who has no negative.

PLAYBOY: Does he have the optics?O’DONNELL: He’s got what he’s got. Look, if you had a Pawlenty who was also dynamic, I’d say, “Oh, the dynamic Pawlenty is going to win. He’s going to beat the undynamic Pawlenty.” There isn’t one.

PLAYBOY: How significant a force is Michele Bachmann?O’DONNELL: She’s another of our media creations. There couldn’t be a Michele Bachmann without a lot of cable news programming chattering about her. In the old-media world, The New York Times would not have spent much time on her. She wouldn’t be getting rewarded in any way for being Michele Bachmann. You didn’t have people talking like that in the early 1990s, to go back to an ancient period, because they would be labeled quacks and ignored by the dominant media, if the dominant media decided to notice them at all. Now that we have all these media outlets and the internet, there’s niche marketing. She’s a niche. Anyone and anything can get on TV now, so it’s possible for all sorts of things to get traction that never would have before. In 1993 a television show about ice-road truckers would have been impossible. Ice Road Truckers is a hit in the world of cable programming now because there are enough people—a million something or whatever it is—who want to watch it, including me. There’s a market for every kind of weird idea in a country of 300 million.

PLAYBOY: You described prime-time cable news, excluding CNN, as op-ed television. Is a danger of op-ed television that viewers may not realize they’re watching commentary from a liberal or conservative point of view? To borrow Fox’s slogan, they may think they’re watching fair and balanced news.O’DONNELL: Which is more dangerous, getting your news exclusively from cable TV or not getting your news?

PLAYBOY: In some cases, maybe propaganda is worse than no news.O’DONNELL: Absolutely nothing can be done about it other than to watch something else. You can watch the Discovery Channel.

PLAYBOY: How has the internet changed discourse in America?O’DONNELL: There are many more public discussions about everything that happens in the world, both for better and worse. The only way you used to be able to get some access to what people were thinking was to listen to call-in talk radio, which I always found fascinating because of exactly that. They were the citizens who were never heard from. Now there are blogs and the internet comment world. The fun thing about it is that people can be much more intemperate and profane than they would ever be calling any radio show other than Howard Stern’s.

PLAYBOY: Let’s tackle a few of the pressing issues. You’ve said we should raise taxes, which is as unpopular a stand as you can take.O’DONNELL: We’re ­living in this absurd tax environment where two UCLA professors who are married to each other are taxed at the same tax rate as Bill Gates and ­Warren Buffett. It’s an absurdly primitive notion of income distribution.

PLAYBOY: Yet the Republicans believe we’re overtaxed.O’DONNELL: Well, they think the government is doing too much. I’m someone who doesn’t think the government is doing too much. My obligation on the liberal side of our politics and our governing policies is to come up with a way to raise revenue to pay for the things I think we should pay for—social services, Social Security, whatever.

PLAYBOY: Apparently you’d go much further even than many liberals. You’ve described yourself as a socialist. Doesn’t that alienate you from most people? During the campaign Obama had to defend himself against those who charged he was a socialist.O’DONNELL: Which he is. He was accused of it by socialists. We’re all socialists, at least any of us who agree Social Security is a good thing. I’m a socialist because I support Social Security and Medicare. They’re socialistic. Everyone who supports these programs is supporting socialism—­including most Republicans.

PLAYBOY: Critics have called Obama’s health care law socialistic. Is it?O’DONNELL: It’s not. It’s the most absurd, ridiculous nonsolution and covers approximately half the people who need to be covered. That’s what the Democratic liberal ideal had become by the time we got to the Obama presidency. Half of them? That’s your idea?

PLAYBOY: Wasn’t that expediency? Isn’t it necessary to compromise to get legislation passed?O’DONNELL: This president began with the notion that the smartest way to solve the health care problem would be to expand Medicare, which is correct. Medicare for people over a certain age works well. It would have taken time to figure out how to make it work for everyone, but it could, and the American public could have understood it, it could have eventually passed, and it wouldn’t have scared so many people.

PLAYBOY: But do you agree that compromise is essential in a country as polarized as ours?O’DONNELL: If you compromise and compromise on what you stand for, then what do you stand for? Nothing. Mario Cuomo was willing to lose his governorship over something not a single Democrat would ever risk an election over again: the death penalty. Does anyone remember the death penalty as a political issue? Guess which side the liberals were on. Guess which side the conservatives were on. The death penalty is not on the list of litmus tests for liberals now. Liberals gave up.

PLAYBOY: For practical reasons? Because polls show most Americans support it?O’DONNELL: It is about being practical, and it is entirely about that for politicians. For Cuomo, a Roman Catholic, no, it’s not about being practical. It’s his agreement with the pope that thou shall not kill. The trick question now for politicians in either party is, Over what would you be willing to lose an election? Bill Clinton would not understand the question. He wouldn’t. Over time, each adjustment you make, especially each moral adjustment you make, moves you closer to being nothing. If you watch the conservative movement on the abortion issue and over the same period of time watch the Democratic Party on the death ­penalty—these two things that people call death—you will notice that one utterly and totally abandoned any attachment to principle and the other gripped the principle tighter and tighter over time. In the 1990s I could have said to Republicans, “Look, can’t you see the country is pro choice now? The country is pretty close to two thirds pro choice. This is a bad formula for you.” However, for many Republicans and virtually all antiabortion Republican voters, this is a deeply important moral issue on which they will not yield. And their refusal to yield on a moral issue over time gives them a moral center around which to organize.

PLAYBOY: Why did Democrats give up on the death penalty?O’DONNELL: There is no lobbying interest against the death penalty. You could be a member of Congress for 40 years and never have one visit from a person lobbying against the death penalty. On the other hand, a vast lobby and a vast voter population have a strong interest in preserving all reproductive rights as they exist now and advancing some of them. It’s why abortion remains an issue for Democrats as it is for Republicans.

PLAYBOY: Will a stalemate remain when it comes to gun control?O’DONNELL: Democrats have been silenced on gun control and ammunition control. By the way, at this time they should be taking on ammunition control, which is more important than gun control.

PLAYBOY: What’s the difference? If you have a car, you need gas. If you have a gun, you need ammunition. They go hand in hand.O’DONNELL: If you want to reduce air pollution in this country, you don’t have to limit the production of automobiles; you have to limit the production of gasoline. There are a couple hundred million guns out there right now that you’ll never get back, but they all need bullets. Ammunition doesn’t last forever; guns do. I don’t care if you have a gun. How much ammunition do you have, and how long is it going to last? Gunpowder deteriorates over time. If I can control your flow of ammunition, those bullets you have now, those 200 bullets, 10 years from now, you’re going to have none. The shooter in Tucson killed as many people as he did because we allow high-­capacity magazines. It used to be that you had to reload after 10 rounds. Not now. Republicans, without a whimper from the Democrats, allowed the ban on those high-capacity magazines to expire. It’s not something they’ll take on. Nor will Obama.

PLAYBOY: You were a writer on The West Wing. How close to the real thing is The West Wing’sdepiction of the Oval Office?O’DONNELL: The Oval Office is a very formal environment, not like on the show. You wouldn’t want to be filming how stiff Oval Office stuff can be. In the end, The West Wing was about entertainment. Watching President Obama at work in the Oval Office wouldn’t necessarily make a show anyone would want to watch.

PLAYBOY: You see the results of Obama in the West Wing. Is he effective when he’s in that room?O’DONNELL: The only way I could render a verdict on that is if I were in the governing chamber with him. I’ve never seen Barack Obama at work. I had moments with President Clinton in the Oval Office when he performed very well—quickly and brilliantly under pressure—and other moments when he was indecisive and slow and afraid of what his wife would think, at least on health care. That was peculiar beyond description: The problem is what the president’s wife thinks?

PLAYBOY: Are you disappointed with Obama’s first two years in office?O’DONNELL: I’m not disappointed in Obama. He’s done a masterful job in many areas. He did a masterful job with his Supreme Court nominations of Sonia Sotomayor and Elena Kagan. Overall, he’s done more than I expected him to do. The fact that the top tax rate did not go back up doesn’t surprise me. They didn’t have the votes to do it. It’s not up to the president. If it were, it would be back up. I get why Guantánamo as a prison facility is still there. Where are you going to put those inmates? We’ve known this about America for a long time: Whatever you want to do is fine, but not in my backyard. If “not in my backyard” applies to anything, it applies to Al Qaeda. Afghanistan is very complex, and the complexities of it change on a daily basis. What is a politician going to do when faced with the responsibility of dealing with those complexities? Obama didn’t run as a peace candidate. People projected onto him things he did not say. They projected onto him the idea that somehow his prosecution of what was going on in Afghanistan would make more sense to people than what was happening under Bush.

PLAYBOY: Has Obama been hamstrung by the midterm elections?O’DONNELL: Yes, and especially now that there are people in Congress whose only agenda is to stop anything from happening. We’ve had a sharp decline in the past 15 years in the education of elected officials. They are being educated in their political and governing views through sloganeering. We’ve produced a class of elected officials who are by far the shallowest in my lifetime. Their entire understanding of what it is they do for a living comes from the talking points put in front of them during their campaign. It’s true of Democrats and Republicans. On the Republican side there are now politicians in office who hate government. You’re electing members of the House of Representatives who are running against government. It’s like saying “I’m running for president of Avis because I hate the car rental business.”

PLAYBOY: Maybe that’s a good thing. Tea Party legislators would respond to that—to use your analogy—they hate the rental car business, and they’re here to fix it.O’DONNELL: The trouble with approaching government from the standpoint of “I hate government” is that you are extremely unlikely to find a better way for government to do anything at all. You are also extremely unlikely to be the persuasive person on the matter of what the government should no longer do. And it’s even worse because of a horrible dynamic that doesn’t allow a Republican to veer from the right, no matter what he or she thinks. Occasionally a Republican would realize Rush Limbaugh had gone way too far and said something absolutely unconscionable and indefensible, and that Republican would say so, and then Rush would immediately discipline that Republican on the radio, and that Republican would apologize, all within a 12-hour news cycle. That policing system is flawless. And when you have a policing system like that on thought, thought stops.

PLAYBOY: If the media are complicit, and Limbaugh and others are the biggest offenders on the right, you have to be included in the list of the biggest offenders on the left.O’DONNELL: I’m not policing thought. The opposite. I encourage thought. I want thoughtfulness. I want people to understand the complexity of the issues. Otherwise nothing meaningful will ever change. I want debate. I want people to be educated enough to have a conversation.

PLAYBOY: But isn’t the reality that MSNBC is simply the left’s answer to Fox News? Isn’t that its raison d’être?O’DONNELL: Not originally. At first MSNBC was trying to be Fox, doing a pathetic imitation of it. In show business you follow the leader, and Fox was the leader. If you have Desperate Housewives, then we’re going to get a housewives show. Fox was this incredible success, just amazing all of us, and MSNBC was trying to imitate it in whatever ways it could, pulling in whatever Republicans it could. The only liberal it hired at that time was named Ron Reagan, and his father used to be president.

PLAYBOY: What changed?O’DONNELL: It was a wonderful creative accident driven by Keith Olbermann. At a certain point in the progress, or lack of progress, of the Iraq war, Keith, who had his show on MSNBC, took a sharp turn to the left, and the ratings skyrocketed. If those ratings had gone down, that sharp left turn would have been stopped. I’m sure the executive class was afraid of it at first, until it saw the ratings reports. Once it did, there was no turning around. Counterprogramming turned out to be exactly what to do.

PLAYBOY: How much do ratings influence the stories you cover? You’ve said you’d like to talk about Chinese currency on the show, yet you’ve also covered Charlie Sheen.O’DONNELL: If a story’s out there, and it’s big and it’s news, we may cover it. On a show I was hosting long before this one, the question came up, “Are we going to do the Lindsay Lohan story tonight? Does this belong in our news mix?” There are holier-than-thou audience members who believe ­Lindsay Lohan doesn’t belong in the news mix, but I said, “Yeah, we can do the Lindsay Lohan story, but we’re not doing any jokes.” This was the same night we were doing a little item about ­Chelsea Clinton’s wedding that weekend, and I noticed these stories had something in common. What we were seeing in ­Chelsea Clinton’s wedding and in the latest Lindsay Lohan saga was a story about American parenting, the risks and possibilities. There were two girls, not of a terribly dissimilar age, who grew up with very difficult parents. If your father is president of the United States, no matter what he’s like, he has made your life extraordinarily difficult. It’s a hard way to grow up, and you have to find your way. And you’re doing it in an age of unbelievably intense media scrutiny. Then when your father misbehaves egregiously, in a way that would be difficult for any daughter to bear, you’re going to have to bear it, knowing that everybody you meet for the rest of your life knows that about your father before they meet you. And there was ­Lindsay Lohan, who is an extraordinary artist, really lovely, in the place she was in—is still in—because her parents chose to put her there. No one can become a child actor without parents saying, “I want my child to become a child actor.” It’s one of the worst things you can do to a child—to put him or her to work that way, to put the burden of movie stardom on a 12-year-old, as she was when she started, and the burden of having hundreds of millions of dollars at stake based on what she does on the set at work tomorrow, to steal childhood from her and then say, “Good luck with adulthood.” It was a terrible, terrible parenting choice. So the story about Lindsay Lohan and Chelsea Clinton that interested me was about their parents. That weekend we were going to see a family, with all the human frailties families have, that did its absolute best under extraordinarily difficult circumstances to provide the best childhood they could for a kid whose father was governor and later president. And then we were watching another couple of parents who cared more about what their child could do for them than they ever cared about what they could do for their child. That’s the story we did.

PLAYBOY: When you spoke about Charlie Sheen, unlike many other shows, which talked about his problems with a sort of prurience and glee, as if it were a joke, you spoke soberly about his mental state and his addiction.O’DONNELL: You can’t grow up Irish in Boston and not know something about addiction. It is one of the plagues of my culture, so I’ve been through these trials with friends and loved ones, and it’s something you can never joke about if you’ve been close to it. There’s no question what you’re looking at because there’s no original behavior. You’re watching a person dying who may or may not die. If you’ve watched someone die that way, there’s only one way to look at it. You’re looking at tragedy, whether it’s an unknown person from my old neighborhood or a celebrity.

PLAYBOY: Now that you’re a celebrity, how does it feel when you’re the subject of speculations and scrutiny by the press?O’DONNELL: I have a perverse relationship to untruths about me: I love them. Every untrue thing said about me publicly means people know less of the truth, and that means I still have my privacy. I once told one of the Kennedy cousins about it. I said, “You know, I love it when they get things completely wrong about me, because it means I still have my privacy.” Like other Kennedys, throughout his life he’d fought against untruths about himself and his family. “You mean it’s a good thing?” It was a revelation for him.

PLAYBOY: What’s a favorite untruth printed about you?O’DONNELL: In the past couple of months it was written that I was some kind of barroom brawler and carouser, which I think is great, especially as it contrasts with my deep dark secret, one I haven’t revealed publicly.

PLAYBOY: What haven’t you wanted people to know?O’DONNELL: My big dark secret is I’ve never had a drink in my life. I’ve never been drunk in my life, and I’ve never taken a drug.

PLAYBOY: That’s your deep dark secret? For most well-known people, that would be the untruth. Why have you hidden it?O’DONNELL: That fact would generate a set of presumptions.

PLAYBOY: Such as?O’DONNELL: It would suggest a tremendous amount of behavioral conservatism, and that’s just not the case. It also would suggest a kind of intolerance, which isn’t the case either. To some people it suggests a kind of discipline that’s absolutely not present. I wish I had that discipline in the face of ice cream. I just don’t have an attraction to the most corrupting and dangerous of consumptions.

PLAYBOY: Did you abstain as a reaction to the alcoholism and addiction you’d seen growing up?O’DONNELL: Every guy was drunk every Friday and Saturday night by the time he was 11 years old. Most of them started around the age of 10. Everybody was drunk by the time they were 11. By the time they were 12, they were seriously drunk every Friday and Saturday night. Some of them never came out of that. But that’s not why I never did it. I simply hated the taste of it. I had nothing against it. I just wouldn’t put something in my mouth that I hated the taste of. It became a mostly faulty girl-getting strategy. My teenage strategy was, “I’ll be the one who’s not puking. Let’s see if that works.” It turns out the girls in my neighborhood weren’t interested in you no matter what you did, so it didn’t work. I was well into adulthood until somebody said to me, “Well, you know, it can help on a date if a girl has had a drink.” And I went, “Hmm, maybe that’s why I’m behind the curve.”

PLAYBOY: Besides your abstinence and lack of luck with girls, how else would you describe your childhood?O’DONNELL: As I said, our neighborhood in Dorchester was almost entirely Irish, and I learned one of the most important things about my culture by watching television. I’m not sure I’ve learned anything since by watching television. When I was a kid, Carroll O’Connor, star of All in the Family, was on The Merv Griffin Show, and they were talking about Irish culture. Merv was asking about when O’Connor went back home to his neighborhood after he’d become a success and said, “That must have been the return of the conquering hero.” O’Connor responded, “Oh, you know, the Irish would much prefer you come back in failure.” On my Little League team, the best thing you could do was get a walk. You didn’t want to strike out; that was embarrassing. But the other embarrassing thing would be to hit a home run.

PLAYBOY: Were your parents hard to please like that?O’DONNELL: They were exceptions. My father was a Boston cop who would sit on the witness stand being cross-examined by lawyers and think, I could do that. And he did. He had to go to school at night, because he didn’t graduate from college, and he became a lawyer. That’s the kind of achievement story that doesn’t belong in my culture. Everyone told him, “You can’t do this. You will fail.”

PLAYBOY: How are you treated now when you go home to your old neighborhood?O’DONNELL: The good thing about my culture’s alienation from achievement is that people are never overly impressed by it. They never think someone has to be looked up to because of what they’ve done occupationally. They take people as they think they are. If you get some fancy job, they’re going to be looking for you to be a jerk about it, and they expect you to be. And if you’re not, then you’re okay.

PLAYBOY: Even after you went off to ­Harvard, worked for a U.S. senator, worked in Hollywood and had your own television show?O’DONNELL: These aren’t people who get impressed. These are people who are never disappointed in a politician because they’re not childish enough to believe what a politician says while running for office. They tend not to be disappointed by a lot of things in life or by a lot of people, because they’re suspicious of appearances and promises. These aren’t people who end up with mortgages they can’t afford in some sort of delusion-driven deals. These are people who tell you what they think, whether you want to hear it or not, which is why this is probably a pretty good job for me. I can say whatever I want about whatever is going on in the world. No one tells me what to say. No one tells me what not to say. No one ever will.